FIELD OF THE INVENTION
This invention is directed to new organic compounds and is particularly concerned with novel 6-phenyl-4H-imidazo[1,2-a][1,4]benzodiazepines, novel intermediates and processes for the production thereof.
The novel compounds and the processes of production therefor can be illustratively represented as follows: ##SPC2##
Alternatively, the synthetic steps for compound V can be carried out as follows: ##SPC3##
The reagents used in the foregoing syntheses were prepared (for scheme I) by the method shown below: ##SPC4##
In an alternative method, the preparation of the reagents (for schemes II and III) proceeds as follows: ##SPC5##
Wherein R.sub.0, R.sub.1, and R.sub.2 are hydrogen, methyl or ethyl; wherein R.sub.3 is hydrogen, chloro or fluoro; wherein R.sub.4 is hydrogen or fluoro; wherein R.sub.5 is hydrogen, chloro, fluoro, bromo, trifluoromethyl or nitro; and wherein R' and R" are hydrogen, methyl or ethyl.
The more preferred compounds of this invention have the formula XXIVB: ##SPC6##
wherein R.sub.6, R.sub.7, and R.sub.2 ' are hydrogen or methyl; wherein R.sub.3 and R.sub.4 are defined as above; and wherein R'.sub.5 is chloro, fluoro or trifluoromethyl, and the pharmacologically acceptable acid addition salts thereof.
The most preferred compounds are of the formula XXIVC: ##SPC7##
wherein R.sub.6 and R.sub.7 are defined as above; R'.sub.3 is hydrogen or chloro; R".sub.5 is chloro or fluoro; and the pharmacologically acceptable acid addition salts thereof.
The process for the production of compounds of formula XXIV comprises: heating a compound of formula I with the novel reagent XIV to yield compound II; reacting compound II with sulfuric acid to obtain compound III; reacting compound III with hydrazine to obtain compound IV and alkylating compound IV with alkylhalides or formaldehyde, sodium cyanoborohydride and acetic acid, to give V, or alternatively reductively alkylating IV in the presence of a suitable catalyst to give a compound of formula XXIV. Compounds IV and V represent the partial scope of the final, desired compounds, otherwise identified as compounds of formula XXIV.
In a similar manner the desired final compounds can be prepared by reacting compound I with the intermediate compound XVIII to give compound VI; reacting compound VI with sodium azide to give compound VII; catalytically hydrogenating VII to give compound VIII; alkylating to give compound IX, and then heating compound IX to between 110.degree. C and 200.degree. C to give compound V, which is a final compound of the invention, encompassed by formula XXIV. Compound VII may be prepared directly by reacting compound I with the intermediate compound XX. Compound IX may also be prepared directly by reacting compound I with the intermediate XXIII (scheme III).
Other variations of these reaction schemes are possible, and will appear in examples. The examples will also show the production of the reactants used in this invention.
The new final compounds of formula XXIV and the pharmacologically acceptable acid addition salts thereof are essentially products which are useful in mammals to counteract anxiety and to produce tranquilization.